Self-assembly of cage structures. Paper 12: The synthesis and crystal structures of 2,5-diazabicyclo[2.2.2]octane-3,6-dione-1,4-dicarboxylic acids and their diesters

Lyssenko, Konstantin А.; Lenev, Denis A.; Kostyanovsky, Remir G.

doi:10.1016/s0040-4020(02)01022-0

Cited by 29 publications

(32 citation statements)

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“…Metal salts of the diacid (Ϯ)-A [9] (Ϯ)-1 to (Ϯ)-3 were prepared in aqueous solution through exchange reactions. The potassium acid salt (Ϯ)-4 was prepared by treatment of A with one equivalent of KOH.…”

Section: Resultsmentioning

confidence: 99%

“…The potassium acid salt (Ϯ)-4 was prepared by treatment of A with one equivalent of KOH. Monosaponification of diester (Ϯ)-B [9] gave compound (Ϯ)-5, which was converted into salts (Ϯ)-6 and (Ϯ)-7 through exchange reactions. All the salts were racemic.…”

Section: Resultsmentioning

confidence: 99%

“…[9] The dianion symmetry in 1 to 3 is close to C 2 (in 1, the dianion occupies the special position on the twofold axis) with some deviation due to variations of the disposition of the CO 2 Ϫ groups and the bicyclic skeleton. In contrast, the symmetry of the monoanionic species in the compounds 4, 6 and 7 cannot exceed C 1 .…”

Section: Resultsmentioning

confidence: 99%

“…[1Ϫ8] In a preceding paper [9] we have shown that functionalized derivaScheme 1. Molecular ''brick wall'' with nonpolar coating (X ϭ CO 2 alkyl) observed in crystal structures of dialkyl DBO-1,4-dicarboxylates, where d 1 is the distance between adjacent molecules in the column and is equal to the corresponding translation (crystal lattice parameter) of the zigzag R 2 2 (8) H-bonded tape columnar packing motif of the purely organic racemic dialkyl 3,6-dioxo-2,5-diazabicyclo [ tives of chiral C 2 -symmetric bicyclic dipeptide, 2,5-diazabicyclo[2.2.2]octane-3,6-dione (DBO), viz.…”

Section: Introductionmentioning

confidence: 99%

“…An attempt to extend the ''brick walls'' into the third dimension (and thus explain the design of the whole crystal structure) through H-bonding, involving carboxylic acid moieties (Scheme 1, X ϭ CO 2 H) failed because of hydrate formation. [9] In the case of competitive H-bonding carbamoyl substituents (X ϭ CONH 2 ), either nanochannels or unbalanced chiral, triply interpenetrated, diamondoid networks form. [19] We therefore tried to use supramolecular forces from another field, metalϪcarboxylate ligand interactions, which it was hoped might direct self-assembly of the desired three-dimensional crystal structure (Scheme 2).…”

Section: Introductionmentioning

confidence: 99%

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Rational Design, Synthesis and Crystal Structure Investigation of Hydrogen‐Bonded Coordination Polymers of Bicyclic Bis‐Lactam Dicarboxylates

Lenev

Kostyanovsky

2003

Eur J Inorg Chem

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The crystal structures of the racemic coordination polymers (±)‐1 to (±)‐4 and the coordination dimers (±)‐6 and (±)‐7, containing molecular “brick walls” with inorganic coatings and molecular “brick walls” with mixed organic‐inorganic coatings, respectively, were predicted and verified on the basis of the zigzag R22(8) H‐bonded tape columnar packing motif of the purely organic racemic dialkyl 3,6‐dioxo‐2,5‐diazabicyclo[2.2.2]octane‐1,4‐dicarboxylates. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Rational Design, Synthesis and Crystal Structure Investigation of Hydrogen‐Bonded Coordination Polymers of Bicyclic Bis‐Lactam Dicarboxylates

Lenev

Kostyanovsky

2003

Eur J Inorg Chem

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Über die Synthese von α‐Azidoestern und geminalen Triaziden

et al. 2014

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Drei einfache Methoden zur Synthese geminaler Triazide werden beschrieben: Ausgehend von 1) 3‐Oxocarbonsäuren, 2) Iodmethylketonen oder 3) terminalen Olefinen gelingt der Aufbau einer Reihe von Triazidomethylketonen unter milden, oxidativen Reaktionsbedingungen mit IBX‐SO3K, einem sulfonierten Derivat der 2‐Iodoxybenzoesäure (IBX), und NaN3 als Azidquelle. Von dieser neuen Verbindungsklasse sind bislang keine Mitglieder beschrieben. Die geminalen Triazide erweisen sich trotz ihres hohen Stickstoffgehalts auch in präparativen Mengen als unerwartet leicht handhabbar (Vorsicht: Explosionsgefahr besteht trotzdem!) und stehen nun erstmals in voller Breite für weitere Untersuchungen zu Reaktivität und Eigenschaften zur Verfügung. Darüber hinaus zeigen wir, wie mit dieser Methode α‐Azidoester, die als Bausteine für Aminosäuren fungieren können, gebildet werden.

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The Synthesis of α‐Azidoesters and Geminal Triazides

et al. 2014

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Three simple methods for the synthesis of geminal triazides are described: Starting from 1) 3-oxocarboxylic acids, 2) iodomethyl ketones, or 3) terminal olefins, a range of triazidomethyl ketones can be constructed under mild oxidative reaction conditions by the use of IBX-SO3 K, a sulfonylated derivative of 2-iodoxybenzoic acid (IBX), and NaN3 as an azide source. This is the first report of representatives of this novel class of triazide compounds: Despite their high nitrogen content, the geminal triazides are easy to handle, even when preparative-scale syntheses are performed. (Caution: These procedures still require protective measures!) The triazides are now broadly available for further studies regarding their properties and reactivity. Furthermore, we show how the method can be used to provide α-azidoesters, which are potential building blocks for amino acids.

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Self-assembly of cage structures. Paper 12: The synthesis and crystal structures of 2,5-diazabicyclo[2.2.2]octane-3,6-dione-1,4-dicarboxylic acids and their diesters

Cited by 29 publications

References 50 publications

Rational Design, Synthesis and Crystal Structure Investigation of Hydrogen‐Bonded Coordination Polymers of Bicyclic Bis‐Lactam Dicarboxylates

Rational Design, Synthesis and Crystal Structure Investigation of Hydrogen‐Bonded Coordination Polymers of Bicyclic Bis‐Lactam Dicarboxylates

Über die Synthese von α‐Azidoestern und geminalen Triaziden

The Synthesis of α‐Azidoesters and Geminal Triazides

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